If you find yourself wanting a terrific view of the famous Key West sunset from the water, you should try the schooner When and If. The people who operate this are fun and lovely. They offer wine tastings or you can bring your own bottle. And they provide a cheese and cracker plate. But the most important thing is the glorious sunset, the song of the conch shell, and pleasant company of the other people sailing with you. The boat is a John Alden schooner, three masted, and magnificently maintained. The sail lasts a couple of hours and is well worth the price.